Mad, Bad and Dangerous to Know, Part One: The Boys

Portrait of Lord Byron by Richard Westall

Every so often you come across a character who, if you met them in real life you’d definitely blacklist. Characters who are dangerous, devious or just plain bad news, and yet also strangely compelling. More so than the noble heroes, these guys are the ones who stay with us long after their story is done. They’re the characters we love to hate to love to hate in spite of ourselves.

To be clear, we’re not talking about the Christian Greys, Edward Rochesters and Maxim de Winters—bad men dressed up as prince charming. No, this isn’t about romance, or something more insidious dressed up as romance. This is about monsters and the way fiction offers us insight into the minds of madmen and the opportunity to flirt with danger.

Henry Winter in The Secret History by Donna Tartt (1992)

You’d think that any undergrad who refuses to engage with television and goes about campus dressing in ‘dark English suits’, carrying an umbrella when it’s not raining, smoking Luckies and speaking ancient Greek would automatically qualify as the biggest hipster d-bag of all time. But Henry Winter pulls it off because Henry Winter is not to be f*%#@d with. Somewhere between dinner parties, tending his garden (what kind of undergrad grows tubers and antique roses?), weekends in the country and teaching himself Sanskrit, he plots and carries out the murder of his best friend. If you can find us a more opaque and compelling young man than Henry, we’d like to meet him.

Humbert Humbert in Lolita by Vladimir Nabokov (1955)

‘You can always count on a murderer for a fancy prose style.’ Indeed, ol’ Hum is a most insidious enchanter. People often and unsurprisingly object to Lolita on the grounds that it deals with pedophilia—Humbert shamelessly carries on a sexual relationship with his teenage step daughter—but the really unnerving thing about this book is Humbert’s narration of his crimes: that he makes the rape of a child read like romance and that, with his playful way with words, he so effortlessly casts the reader under his spell.

Dean Moriarty in On the Road by Jack Kerouac (1957)

Modelled after Neal Cassady (and still named Neal Cassady in the original scroll), Dean Morriarty is your go-to guy for reckless fun. Pill poppin’, hot wheelin’ man with a plan that’s guaranteed to end in disaster, he’ll show you a good time then leave you stranded. He’s a true wayfarer, rebel and the spirit of the beat generation.

Tom Ripley in The Talented Mr. Ripley by Patricia Highsmith (1955)

A young working class man with expensive tastes and a gift for mimicry, it takes Tom mere pages to rise from the slums of New York to the moneyed Italian resort town of Mongibello. If nothing else, you’ve got to admire Ripley’s ambition. Amoral and asexual, Tom is a sociopathic aesthete who will stop at nothing, least of all murder, to keep up appearances.

Boris in The Goldfinch by Donna Tartt (2013)

From a fledgling teenage drug lord in suburban Las Vegas to international art forger, Boris is Theo Decker’s larger than life sidekick. He’s a smooth talker who oozes charm with his Russian syntax and Aussie accent, and he’s guaranteed to know a guy who can help you out—whatever you need, no problem. But the plan is always a little more complicated and a whole lot more illegal than he lets on, but riding with Boris is more than worth the gaol time.

Lestat de Lioncourt in The Vampire Chronicles by Anne Rice (1976)

Revelling in excess and as hungry for meaning as he is for pleasure, Lestat is the vampire who marched from the Gothic shadows that made monsters of his kind and refashioned himself a rock god. Forget Edward Cullen and Eric Northman, Lestat is the Brat Prince you want to stay up late with. Just quit reading after Queen of the Damned (1988)—you can have too much of a good thing.

Alex in A Clockwork Orange by Anthony Burgess (1962)

A teenager with a taste for ‘ultra violence’ and classical music, particularly from the ‘Lovely Ludwig Van’, Alex is a charming sociopath whose often childlike Nadsat argot creates an unsettling juxtaposition with his actions. His crimes are heinous, but so are the crimes committed against him, and he remains a favourite anti-hero of twentieth century literature.

Patrick Bateman in American Psycho by Bret Easton Ellis (1991)

Bateman more than lives up to his title and there are large chunks of this book that you really shouldn’t mix with food. In fact, we’re struggling to think of a character more monstrous than this guy because rats and acid. But he’s also compelling and, in some ways, the most likeable—or at least relatable— figure in Ellis’s hyper real playground of materialism and excess.

Dorian Grey in The Picture of Dorian Gray by Oscar Wilde (1891)

Poster boy for hedonism and walking cautionary tale that beauty is only skin deep, Dorian Gray is possessed of an irresistible duality: art and destruction, murder and creation. No anti-hero has looked this good since Narcissus.

Ned Kelly in True History of The Kelly Gang by Peter Carey (2000)

Depending who you ask, Ned Kelly is either one of Australia’s greatest villains or a national hero—our very own Robin Hood. In his Man Booker Prize winning novel, Carey very much comes down in favour of old Ned, not excusing his crimes but weaving a colourful story in the form of the bushranger’s diary to explain his motives and attempt to find the man behind the mask.

Jean-Baptiste Grenouille in Perfume: The Story of a Murderer by Patrick Süskind (1985)

A murderer with a preternatural sense of smell, Grenouille is a truly unique anti-hero who abandons himself fully to sensory pleasure and the pursuit of his desires. Even if he were not such a fascinating character who manages time and again to climb from ruin to riches, his experience of the world through his olfactory system would be enough to make him one of literature’s more intriguing characters.

Tyler Durden in Fight Club by Chuck Palahniuk (1996)

He’s the devil on your shoulder, a soldier against corporate America and architect of Project Mayhem. Tyler is the guy you wish you had the gumption to be. In theory. Sort of. He is anarchy—antithesis to the status quo—and he is hell bent on shaking you out of your pathetic cookie-cutter life.

Lou Ford in The Killer Inside Me by Jim Thompson (1952)

Town deputy sherif by day, cold-blooded killer by night: Lou Ford isn’t a guy you want to invite round for dinner, but he is one hell of a storyteller. He cultivates a dull outward persona, boring the local townsfolk into complacency while secretly indulging his depraved desires. But like many psychopaths, he’s not so smart as he thinks and it isn’t long before he starts to make mistakes.

Hannibal Lecter in Red Dragon, et al by Thomas Harris (1981)

The best kind of serial killer is a smart serial killer, and Dr. Lecter is the perfect monster, sporting sophistication and barbarism in equal measure. In the latter Hannibal books, Harris takes us inside Lecter’s mind, but it’s in the earlier books, Red Dragon and The Silence of the Lambs (1988), where the extent of his intelligence remains unknown, that he is at his most terrifying and compelling. There is something wonderfully dark and playful about a cannibal who insists on perfect table etiquette.

Daniel Kelly in Barracuda by Christos Tsiolkas (2013)

Daniel Kelly is a difficult character to ride with. His words come at you like fists—a lifetime of anger and disappointment let out in five hundred unrelenting pages. He’s an angry young man with a chip on his shoulder and everything is someone else’s fault. But get past the initial wave of his rage and Danny reveals himself as one of the most complex and layered characters in recent Australian literature.